HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 89690351, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Oxocyclobutane-1-carboxylic acid | HCID 4913358 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 5-Bromo-N1-methylbenzene-1,2-diamine | HCID 12198270 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89690351 | HCID 89690351 | 98.9% |
Reaction Steps
To a stirred solution of 3-oxocyclobutanecarboxylic acid (1.1 g) in DMF (50 ml) were added HATU (5.7 g) and N,N-diisopropylethylamine (4.2 ml) at 0° C., and the mixture was allowed to warm to room temperature for 30 min. A solution of 4-bromo-N2-methylbenzene-1,2-diamine (2.0 g) in DMF (2 ml) was added, and the resulting mixture was stirred at room temperature for 18 h. The mixture was concentrated in vacuo and diluted with DCM. The mixture was washed with saturated NH4Cl solution, saturated NaHCO3 solution and brine successively, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (hexane/EtOAc) to afford the title compound (2.7 g) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-6ee308dfcf1842678c012ee650986195 |
| Source note | uspto-grants-2016_06 |